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Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate

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Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate Basic information
Synthesis
Product Name:Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate
Synonyms:METHYL FLUOROSULPHONYLDIFLUOROACETATE;METHYL 2,2-DIFLUORO-2-(FLUOROSULFONYL)ACETATE;FLUOROSULFONYL(DIFLUORO)ACETIC ACID METHYL ESTER;uoro-2-(fL;uorosuL;METHYL 2,2-DIFLUORO-2-(FLUOROSULFONYL)-A;FLUOROSULFONYL ACETIC ACID METHYL ESTER;Methyl fluorosulphonyldifluoroacetate 97%
CAS:680-15-9
MF:C3H3F3O4S
MW:192.11
EINECS:808-179-4
Product Categories:Small molecule;Fluorinated Building Blocks;Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds;Synthetic Organic Chemistry;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds
Mol File:680-15-9.mol
Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate Structure
Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate Chemical Properties
Boiling point 117-118 °C(lit.)
density 1.509 g/mL at 25 °C(lit.)
refractive index n20/D 1.351(lit.)
Fp 118 °F
storage temp. 2-8°C(protect from light)
form liquid
Specific Gravity1.52
color colorless to yellow
BRN 1812896
InChIInChI=1S/C3H3F3O4S/c1-10-2(7)3(4,5)11(6,8)9/h1H3
InChIKeyGQJCAQADCPTHKN-UHFFFAOYSA-N
SMILESC(OC)(=O)C(F)(F)S(F)(=O)=O
CAS DataBase Reference680-15-9(CAS DataBase Reference)
EPA Substance Registry SystemAcetic acid, 2,2-difluoro-2-(fluorosulfonyl)-, methyl ester (680-15-9)
Safety Information
Hazard Codes C,Xi
Risk Statements 10-34
Safety Statements 26-36/37/39-45-16
RIDADR UN 2920 8/PG 2
WGK Germany 3
10-21
Hazard Note Irritant
TSCA No
HazardClass 3.2
PackingGroup III
HS Code 29159000
Storage Class3 - Flammable liquids
Hazard ClassificationsFlam. Liq. 3
Skin Corr. 1B
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate Usage And Synthesis
Synthesis

Synthetic Route of Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate

Equip a 1000 mL oven-dried three-necked round-bottom flask with a magnetic stir bar, an attached constant-pressure funnel, and a gas outlet. Connect the gas outlet to an empty 500 mL spare trap, which is then connected to the outlet of an inverted glass funnel located directly above a 1000 mL beaker containing 120 g NaOH in 600 mL of water. Add anhydrous methanol (160 g) to the flask. Add tetrafluoroethane-β-sulfonyl lactone (440 g) dropwise to the mixture through a feeding funnel with stirring. Cool the mixture in an ice bath for 3 hours. After the addition is complete, gradually heat the reaction mixture to room temperature. Stir the mixture overnight at room temperature.

After purging with nitrogen for 1 hour to completely remove residual HF from the system, the resulting reaction mixture was washed with water (2 × 400 mL) and brine (2 × 400 mL) to remove residual methanol. The organic phase was collected and dried over anhydrous sodium sulfate. After filtration, the crude product was purified by distillation.
Chemical Propertiesclear colorless to yellow liquid
UsesEfficient reagent for the trifluoromethylation of aryls and difluorocyclopropanation of alkenes.
UsesMethyl 2,2-difluoro-2-(fluorosulfonyl)acetate is a useful reagent for the trifluoromethylation of alkyl halides. It is also broadly applicable reagent for perfluoroalkylations for aryl iodides and bromides.
reaction suitabilityreaction type: click chemistry
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